An Efficient Method for the Reductive Conversion of Acyclic Esters to Ethers Via a TMS-Protected Acetal
Chemistry and Biochemistry
We report an efficient two step process for the reduction of non-aromatic esters to the corresponding ethers via the intermediate TMS-protected acetal. The acetal formed after the first step can be carried on directly to the subsequent reduction to the ether without purification. The ester reduction step was monitored using in-situ ReactIR for disappearance of the CO peak, allowing for the exact determination of time and equivalents of the reducing agent. Furthermore, use of TMS-imidazole to form the acetal has allowed us to dramatically reduce the overall reaction time required for the two step procedure.
Kelley, S. A.,
Hood, J. A.,
Pigza, J. A.
(2017). An Efficient Method for the Reductive Conversion of Acyclic Esters to Ethers Via a TMS-Protected Acetal. Tetrahedron Letters, 58(31), 3024-3027.
Available at: https://aquila.usm.edu/fac_pubs/15081